Synthesis and characterization of alternating poly(amide urethane)s from ε-caprolactam, amino alcohols, and diphenyl carbonate

Abstract

Alternating poly(amide urethane)s from ε-caprolactam, amino alcohols H2N–(CH2)x–OH (x=2–6), and diphenyl carbonate were prepared by polycondensation of α-hydroxy-ω-O-phenylurethanes 4a-e. The degree of oligomerization was adjusted by the conversion. Oligomers with two or three O-phenylurethane end groups and predetermined molecular weight were prepared by polycondensation of the α-hydroxy-ω-O-phenylurethanes 4a-e in the presence of comonomers with O-phenylurethane end groups in a given concentration. In order to prepare oligomers with hydroxyl and carboxyl groups at both chain ends suitable for coupling reactions, chain analogous reactions were performed with amino acids and amino alcohols. The microstructure of the polymers and the nature of end groups was determined by means of 1H NMR spectroscopy and the molecular weights were determined by means of gel permeation chromatography. The poly(amide urethane)s 5a-e prepared are semicrystalline materials with melting points between 150 and 200 °C.